When Andrew was transferred to Chicago from Miami for work, Andrew's dad had a premonition that Andrew would meet a nice Midwestern girl in the Windy City. Soon after, Andrew and Stacey first met, and they bonded over their mutual love for candy and their mutual hatred for convention.

A few weeks later, Stacey was supposed to go on a date with another gentleman, and Andrew was supposed to spend the weekend in Miami. Andrew boarded his flight and started heading south, but halfway to Miami, the captain turned the plane around because fate. Andrew texted Stacey from O'Hare that his plans had changed, and Stacey immediately canceled her other date. The two were quickly inseparable.

After Andrew moved back to Miami, Stacey spent four months studying for the Florida bar examination, which she took in February 2015. Andrew traveled to Tampa to stay in a hotel with Stacey while she took the test. Each day, Andrew dropped Stacey off at the test, brought lunch, and picked her up. A few days after the ordeal was done, Andrew proposed at Next Restaurant in Chicago, at dinner with Brooke, Stacey's sister, and Mike, Brooke's boyfriend. The four celebrated the engagement and Brooke and Stacey's birthdays through the rest of the weekend. In August 2015, Stacey moved to Miami to be with Andrew.